Licofelone
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Hodoodo CAT#: H326950

CAS#: 156897-06-2

Description: Licofelone, also known as ML-3000, is a dual COX/LOX inhibitor potentially for the treatment of osteoarthritis. Licofelone is both an analgesic and an anti-inflammatory. Inhibition of 5-LOX may reduce the gastrointestinal toxicity associated with other non-steroidal anti-inflammatory drugs, which only inhibit COX (cyclooxygenase). Licofelone is the first drug to inhibit both.

Chemical Structure

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Licofelone
CAS# 156897-06-2
Instruction

Theoretical Analysis

Hodoodo Cat#: H326950
Name: Licofelone
CAS#: 156897-06-2
Chemical Formula: C23H22ClNO2
Exact Mass: 379.13
Molecular Weight: 379.884
Elemental Analysis: C, 72.72; H, 5.84; Cl, 9.33; N, 3.69; O, 8.42

Price and Availability

Size Price Availability Quantity
5mg USD 350 2 Weeks
10mg USD 600 2 Weeks
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Synonym: Licofelone; ML-3000; ML 3000; ML3000.

IUPAC/Chemical Name: (6-(4-Chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid

InChi Key: UAWXGRJVZSAUSZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H22ClNO2/c1-23(2)13-19-22(15-6-4-3-5-7-15)21(16-8-10-17(24)11-9-16)18(12-20(26)27)25(19)14-23/h3-11H,12-14H2,1-2H3,(H,26,27)

SMILES Code: O=C(O)CC1=C(C2=CC=C(Cl)C=C2)C(C3=CC=CC=C3)=C4N1CC(C)(C)C4

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 379.88 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Payandemehr B, Khoshneviszadeh M, Varastehmoradi B, Gholizadeh R, Bahremand T, Attar H, Bahremand A, Dehpour AR. A COX/5-LOX Inhibitor Licofelone Revealed Anticonvulsant Properties Through iNOS Diminution in Mice. Neurochem Res. 2015 Sep;40(9):1819-28. doi: 10.1007/s11064-015-1669-z. Epub 2015 Jul 28. PubMed PMID: 26216049.

2: Balansky R, Ganchev G, Iltcheva M, Nikolov M, Maestra SL, Micale RT, D'Agostini F, Steele VE, De Flora S. Modulation by licofelone and celecoxib of experimentally induced cancer and preneoplastic lesions in mice exposed to cigarette smoke. Curr Cancer Drug Targets. 2015;15(3):188-95. PubMed PMID: 25687474.

3: Kumar A, Sharma S, Prashar A, Deshmukh R. Effect of licofelone--a dual COX/5-LOX inhibitor in intracerebroventricular streptozotocin-induced behavioral and biochemical abnormalities in rats. J Mol Neurosci. 2015 Mar;55(3):749-59. doi: 10.1007/s12031-014-0414-4. Epub 2014 Sep 10. PubMed PMID: 25204299.

4: Zhang K, Zhao J, Su W, Lu R, Lv P. Immunomodulatory effectiveness of licofelone in preventing epidural fibrosis in post-laminectomy rat. Eur J Orthop Surg Traumatol. 2015 Jul;25 Suppl 1:S63-8. doi: 10.1007/s00590-014-1534-9. Epub 2014 Sep 9. PubMed PMID: 25200318.

5: Madka V, Mohammed A, Li Q, Zhang Y, Patlolla JM, Biddick L, Lightfoot S, Wu XR, Steele V, Kopelovich L, Rao CV. Chemoprevention of urothelial cell carcinoma growth and invasion by the dual COX-LOX inhibitor licofelone in UPII-SV40T transgenic mice. Cancer Prev Res (Phila). 2014 Jul;7(7):708-16. doi: 10.1158/1940-6207.CAPR-14-0087. Epub 2014 May 2. PubMed PMID: 24795386; PubMed Central PMCID: PMC4310686.

6: Kus G, Oztopcu-Vatan P, Uyar R, Kabadere S. Cytotoxic and apoptotic functions of licofelone on rat glioma cells. Acta Biol Hung. 2013 Dec;64(4):438-52. doi: 10.1556/ABiol.64.2013.4.4. PubMed PMID: 24275590.

7: Kabadere S, Kus G, Uyar R, Oztopcu-Vatan P. Licofelone abolishes survival of carcinogenic fibroblasts by inducing apoptosis. Drug Chem Toxicol. 2014 Jan;37(1):1-7. doi: 10.3109/01480545.2013.806525. Epub 2013 Jul 8. PubMed PMID: 23834160.

8: Dulin JN, Karoly ED, Wang Y, Strobel HW, Grill RJ. Licofelone modulates neuroinflammation and attenuates mechanical hypersensitivity in the chronic phase of spinal cord injury. J Neurosci. 2013 Jan 9;33(2):652-64. doi: 10.1523/JNEUROSCI.6128-11.2013. PubMed PMID: 23303944; PubMed Central PMCID: PMC3586230.

9: Kumar A, Vashist A, Kumar P, Kalonia H, Mishra J. Potential role of licofelone, minocycline and their combination against chronic fatigue stress induced behavioral, biochemical and mitochondrial alterations in mice. Pharmacol Rep. 2012;64(5):1105-15. PubMed PMID: 23238467.

10: Dulin JN, Moore ML, Grill RJ. The dual cyclooxygenase/5-lipoxygenase inhibitor licofelone attenuates p-glycoprotein-mediated drug resistance in the injured spinal cord. J Neurotrauma. 2013 Feb 1;30(3):211-26. doi: 10.1089/neu.2012.2587. Epub 2013 Jan 23. PubMed PMID: 22947335; PubMed Central PMCID: PMC3565554.

11: Wu YJ, Xue M, Chen H. Licofelone inhibits interleukin-18-induced pro-inflammatory cytokine release and cellular proliferation in human mesangial cells. Basic Clin Pharmacol Toxicol. 2012 Sep;111(3):166-72. doi: 10.1111/j.1742-7843.2012.00882.x. Epub 2012 Apr 11. PubMed PMID: 22433003.

12: Tavolari S, Munarini A, Storci G, Laufer S, Chieco P, Guarnieri T. The decrease of cell membrane fluidity by the non-steroidal anti-inflammatory drug Licofelone inhibits epidermal growth factor receptor signalling and triggers apoptosis in HCA-7 colon cancer cells. Cancer Lett. 2012 Aug 28;321(2):187-94. doi: 10.1016/j.canlet.2012.02.003. Epub 2012 Feb 14. PubMed PMID: 22343320.

13: Mohammed A, Janakiram NB, Li Q, Choi CI, Zhang Y, Steele VE, Rao CV. Chemoprevention of colon and small intestinal tumorigenesis in APC(Min/+) mice by licofelone, a novel dual 5-LOX/COX inhibitor: potential implications for human colon cancer prevention. Cancer Prev Res (Phila). 2011 Dec;4(12):2015-26. doi: 10.1158/1940-6207.CAPR-11-0233. Epub 2011 Sep 1. PubMed PMID: 21885812; PubMed Central PMCID: PMC3232346.

14: Liu W, Zhou J, Liu Y, Liu H, Bensdorf K, Guo C, Gust R. Licofelone-nitric oxide donors as anticancer agents. Arch Pharm (Weinheim). 2011 Aug;344(8):487-93. doi: 10.1002/ardp.201000397. Epub 2011 Jun 16. PubMed PMID: 21681808.

15: Sharma S, Lee J, Zhou J, Steele VE. Chemopreventive efficacy and mechanism of licofelone in a mouse lung tumor model via aspiration. Cancer Prev Res (Phila). 2011 Aug;4(8):1233-42. doi: 10.1158/1940-6207.CAPR-10-0117. Epub 2011 May 11. PubMed PMID: 21562034; PubMed Central PMCID: PMC3151334.

16: Kumar P, Kalonia H, Kumar A. Role of LOX/COX pathways in 3-nitropropionic acid-induced Huntington's disease-like symptoms in rats: protective effect of licofelone. Br J Pharmacol. 2011 Sep;164(2b):644-54. doi: 10.1111/j.1476-5381.2011.01418.x. PubMed PMID: 21486276; PubMed Central PMCID: PMC3188893.

17: Liu W, Zhou J, Bensdorf K, Zhang H, Liu H, Wang Y, Qian H, Zhang Y, Wellner A, Rubner G, Huang W, Guo C, Gust R. Investigations on cytotoxicity and anti-inflammatory potency of licofelone derivatives. Eur J Med Chem. 2011 Mar;46(3):907-13. doi: 10.1016/j.ejmech.2011.01.002. Epub 2011 Jan 11. PubMed PMID: 21295381.

18: Kalonia H, Kumar P, Kumar A. Licofelone attenuates quinolinic acid induced Huntington like symptoms: possible behavioral, biochemical and cellular alterations. Prog Neuropsychopharmacol Biol Psychiatry. 2011 Mar 30;35(2):607-15. doi: 10.1016/j.pnpbp.2011.01.003. Epub 2011 Jan 13. PubMed PMID: 21237233.

19: Gupta A, Kumar A, Kulkarni SK. Licofelone attenuates MPTP-induced neuronal toxicity: behavioral, biochemical and cellular evidence. Inflammopharmacology. 2010 Oct;18(5):223-32. doi: 10.1007/s10787-010-0052-6. Epub 2010 Aug 11. PubMed PMID: 20697819.

20: Raynauld JP, Martel-Pelletier J, Bias P, Laufer S, Haraoui B, Choquette D, Beaulieu AD, Abram F, Dorais M, Vignon E, Pelletier JP; Canadian Licofelone Study Group. Protective effects of licofelone, a 5-lipoxygenase and cyclo-oxygenase inhibitor, versus naproxen on cartilage loss in knee osteoarthritis: a first multicentre clinical trial using quantitative MRI. Ann Rheum Dis. 2009 Jun;68(6):938-47. doi: 10.1136/ard.2008.088732. Epub 2008 Jul 23. PubMed PMID: 18653484.